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IUPAC name
3α-Hydroxypregn-4-en-20-one
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Systematic IUPAC name
1-[(1S,3aS,3bS,7R,9aR,9bS,11aS)-7-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one | |
| Other names
3α-Dihydroprogesterone
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| Identifiers | |
3D model (
JSmol)
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| ChemSpider | |
PubChem
CID
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| UNII | |
CompTox Dashboard (
EPA)
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| Properties | |
| C21H32O2 | |
| Molar mass | 316.485 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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3α-Dihydroprogesterone (3α-DHP), also known as 3α-hydroxyprogesterone, as well as pregn-4-en-3α-ol-20-one, is an endogenous neurosteroid. [1] It is biosynthesized by 3α-hydroxysteroid dehydrogenase from progesterone. [1] 3α-DHP has been found to act as a positive allosteric modulator of the GABAA receptor and is described as being as active as allopregnanolone in regard to this action. [1] In accordance, it has anxiolytic effects in animals. [2] 3α-DHP has also been found to inhibit the secretion of follicle-stimulating hormone (FSH) from the rat pituitary gland, demonstrating possible antigonadotropic properties. [1] Unlike the case of most other inhibitory neurosteroids, 3α-DHP production is not blocked by 5α-reductase inhibitors like finasteride. [1] No data were available on the progestogenic activity of 3α-DHP as of 1977. [3] Levels of 5α-DHP have been quantified. [4]
Chemistry
See also
References
- ^ a b c d e Neurosteroids and Brain Function. Academic Press. 12 December 2001. pp. 484–. ISBN 978-0-08-054423-6.
- ^ Kavaliers, Martin; Wiebe, John P.; Galea, Liisa A.M. (1 May 1994). "Reduction of predator odor-induced anxiety in mice by the neurosteroid 3 alpha-hydroxy-4-pregnen-20-one (3 alpha HP)". Brain Research. 645 (1–2): 325–329. doi: 10.1016/0006-8993(94)91667-5. ISSN 0006-8993. PMID 7914815. S2CID 53259529. Wikidata Q48124086.
- ^ Junkermann H, Runnebaum B, Lisboa BP (July 1977). "New progesterone metabolites in human myometrium". Steroids. 30 (1): 1–14. doi: 10.1016/0039-128x(77)90131-3. PMID 919010. S2CID 28420255.
- ^ Trabert B, Falk RT, Stanczyk FZ, McGlynn KA, Brinton LA, Xu X (September 2015). "Reproducibility of an assay to measure serum progesterone metabolites that may be related to breast cancer risk using liquid chromatography-tandem mass spectrometry". Horm Mol Biol Clin Investig. 23 (3): 79–84. doi: 10.1515/hmbci-2015-0026. PMC 4966666. PMID 26353176.